IP Library Granted Patent US 9,663,515
Granted Patent B2
US 9,663,515 · App. 14/933,524 · Granted May 30, 2017

Dihydropyrrolopyridine inhibitors of ROR-gamma

Inventors: David A. Claremon (Maple Glen, PA); Lawrence Wayne Dillard (Yardley, PA); Chengguo Dong (Staten Island, NY); Yi Fan (Doylestown, PA); Stephen D. Lotesta (Burlington, NJ); Andrew Marcus (Media, PA); Suresh B. Singh (Kendall Park, NJ); Colin M. Tice (Maple Glen, PA); Jing Yuan (Lansdale, PA); Wei Zhao (Germantown, MD); Linghang Zhuang (Chalfont, PA)
Assignee: Vitae Pharmaceuticals, Inc.
C07D471/04
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Quick Facts
Patent No.
US 9,663,515
App. No.
14/933,524
Granted
May 30, 2017
Kind
B2
Abstract

Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by RORγ. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.

Claims (32)

1. A compound of the Formula:

or a pharmaceutically acceptable salt thereof, wherein

R 2 is (C 1 -C 3 )alkyl, hydroxy(C 1 -C 3 )alkyl, halo(C 1 -C 3 )alkyl, benzyl, (C 1 -C 3 )alkoxy(C 1 -C 3 )alkyl, tetrahydropyranyl, or —CH 2 -tetrahydropyranyl;

Cy 1 is phenyl or pyridyl, each substituted with (C 1 -C 3 )alkylsulfonyl;

Cy 2 is cyclohexyl or tetrahydropyranyl, each optionally substituted with one or more groups selected from halo and halo(C 1 -C 3 )alkyl;

R 7 is hydrogen, (C 1 -C 3 )alkyl-O—(C 1 -C 3 )alkyl, aminocarbonyl-O—(C 1 -C 3 )alkyl, (C 1 -C 3 )alkylaminocarbonyl-O—(C 1 -C 3 )alkyl, di(C 1 -C 3 )alkylaminocarbonyl-O—(C 1 -C 3 )alkyl, or hydroxycarbonyl(C 1 -C 3 )alkyl-O—(C 1 -C 3 )alkyl; and

R 8 is (C 1 -C 3 )alkyl-O—(C 1 -C 3 )alkyl, aminocarbonyl-O—(C 1 -C 3 )alkyl, (C 1 -C 3 )alkylaminocarbonyl-O—(C 1 -C 3 )alkyl, di(C 1 -C 3 )alkylaminocarbonyl-O—(C 1 -C 3 )alkyl, or hydroxycarbonyl(C 1 -C 3 )alkyl-O—(C 1 -C 3 )alkyl.

2. The compound of claim 1 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 2 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 3 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 4 , wherein R 2 is (C 1 -C 3 )alkyl.

6. The compound of claim 5 , wherein Cy 2 is cyclohexyl or tetrahydropyranyl, each substituted with halo(C 1 -C 3 )alkyl.

7. The compound of claim 6 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof, wherein

X is CH or N;

Y is O or CH 2 ;

R 9 is halo(C 1 -C 3 )alkyl; and

R 10 is (C 1 -C 3 )alkylsulfonyl.

8. The compound of claim 7 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

9. The compound of claim 8 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

10. The compound of claim 9 , wherein R 9 is CF 3 ; and R 10 is SO 2 Et or SO 2 Me.

11. The compound of claim 10 , wherein R 8 is —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , —CH 2 OC(O)NH 2 , or —CH 2 OCH 2 COOH.

12. The compound of claim 11 , wherein R 8 is —CH 2 OCH 3 .

13. The compound of claim 1 , wherein the compound is selected from

or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

15. A method of treating Crohn's disease, psoriasis, psoriatic arthritis (PsA), inflammatory bowel disease (IBD), rheumatoid arthritis, juvenile rheumatoid arthritis, systemic lupus erythematosus (SLE), multiple sclerosis, ankylosing spondylitis, and asthma in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

Assignments (2)
CHANGE OF NAME Recorded Mar 20, 2019
From: VITAE PHARMACEUTICALS, INC.
To: VITAE PHARMACEUTICALS, LLC
Reel/Frame 050150/0044 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2015
From: CLAREMON, DAVID A.; DILLARD, LAWRENCE WAYNE; DONG, CHENGGUO; FAN, YI; LOTESTA, STEPHEN D.; MARCUS, ANDREW; SINGH, SURESH B.; TICE, COLIN M.; YUAN, JING; ZHAO, WEI; ZHUANG, LINGHANG
To: VITAE PHARMACEUTICALS, INC.
Reel/Frame 037155/0563 →
Continuity (2)
Provisional Application 62075602 · Nov 5, 2014
Related Publication 20160122345A1 · May 5, 2016